title: Structure and absolute stereochemistry of the anticancer agent EBC-23 from the Australian rainforest.
abstract: EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.
authors.affiliation: School of Molecular and Microbial Sciences, University of Queensland, Brisbane, Queensland, Australia.
authors.forename: Lin
authors.initials: L
authors.lastname: Dong
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Gordon
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Grange
authors.forename: Jenny
authors.initials: J
authors.lastname: Johns
authors.forename: Peter G
authors.initials: PG
authors.lastname: Parsons
authors.forename: Achim
authors.initials: A
authors.lastname: Porzelle
authors.forename: Paul
authors.initials: P
authors.lastname: Reddell
authors.forename: Heiko
authors.initials: H
authors.lastname: Schill
authors.forename: Craig M
authors.initials: CM
authors.lastname: Williams
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001315:Australia; D027424:Cinnamomum / Q000737:chemistry; D002980:Climate; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D011891:Rain; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014197:Trees
chemical_list: D000970:Antineoplastic Agents; C534557:EBC-23; D011714:Pyrans; D013141:Spiro Compounds